2-phenyl-1-(phenylthio)propan-2-ol | 78349-02-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-phenyl-1-(phenylthio)propan-2-ol
• 英文别名: 2-Phenyl-1-phenylsulfanylpropan-2-ol
• CAS: 78349-02-7
• 化学式: C₁₅H₁₆OS
• 分子量: 244.357
• InChiKey: XJJFFRMKKIWSLN-UHFFFAOYSA-N

物化性质

• 沸点：
  394.7±35.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  trimethyl-(2-phenyl-1-phenylsulfanylpropan-2-yl)oxysilane 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 2-phenyl-1-(phenylthio)propan-2-ol
  参考文献：
  名称：

  Hosomi, Akira; Ogata, Koichiro; Hoashi, Koichiro, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 9, p. 3736 - 3738

  摘要：

  DOI：

文献信息

• Aerial dioxygen activation <i>vs.</i> thiol–ene click reaction within a system
  作者：Khokan Choudhuri、Arkalekha Mandal、Prasenjit Mal

  DOI：10.1039/c8cc01359d

  日期：——

  Markovnikov or anti-Markovnikov selective thiol–ene click (TEC) reactions and the synthesis of β-hydroxysulfides via aerial dioxygen activation are prevalent C–S bond forming reactions of styrenes and thiophenols. Herein, by choosing appropriate environments using solvents with additives or neat conditions, any one of these three reactions was achieved exclusively in excellent yields.

  Markovnikov或反Markovnikov选择性硫醇-烯点击（TEC）反应和通过空中双氧活化合成β-羟基硫化物是苯乙烯和硫酚的常见C-S键形成反应。在本文中，通过使用具有添加剂的溶剂或在纯净条件下选择合适的环境，这三个反应中的任何一个仅以优异的收率实现。
• Selectivities in the Reactions of Alkyl-, Aryl- and Heterosubstituted Organotitanium Compounds Preliminary Communication
  作者：Beat Weidmann、Leo Widler、Alan G. Olivero、Christopher D. Maycock、Dieter Seebach

  DOI：10.1002/hlca.19810640136

  日期：1981.2.4

  Solutions of the title compounds R-Ti(OR′)3 (1) are generally available from organolithium (or magnesium) derivatives according to equation 1. It is shown (Table 1) that some heterosubstituted organotitanium compounds are more stable thermally than their lithium counterparts. The reagents 1 are highly selective carbonylophiles (Tables 1 and 2), their reactivity can be modified by variation of the R′O-group

  标题化合物R-Ti（OR'）3（1）的溶液通常可从等式1的有机锂（或镁）衍生物获得。显示（表1）某些杂取代的有机钛化合物比其锂的热稳定性更高同行。试剂1是高度选择性的亲羰基化合物（表1和2），其反应性可通过改变R'O-基团（表3）和手性（S）-2-甲基-1-丁氧基进行对映选择性修饰。可以实现加法[equ。2]。
• Stereoselective synthesis of 3,4-di-substituted mercaptolactones via photoredox-catalyzed radical addition of thiophenols
  作者：Farzana Kouser、Vijay Kumar Sharma、Masood Rizvi、Shaista Sultan、Neha Chalotra、Vivek K. Gupta、Utpal Nandi、Bhahwal Ali Shah

  DOI：10.1016/j.tetlet.2018.04.046

  日期：2018.5

  A visible light mediated radical addition of thiophenols on 4-phenylbut-3-enoic acids to give diastereoselective synthesis of 3,4-disubstituted γ-lactones is reported. The reaction precludes the conventional prerequisite of conjugate addition. Furthermore, the lactones were successfully utilized in the synthesis of γ-ketoamides.

  报道了在4-苯基丁-3-烯酸上可见光介导的苯酚的自由基加成，以非对映选择性合成3,4-二取代的γ-内酯。该反应排除了缀合物添加的常规先决条件。此外，内酯已成功用于γ-酮酰胺的合成。
• Solvent-mediated switching between oxidative addition and addition–oxidation: access to β-hydroxysulfides and β-arylsulfones by the addition of thiols to olefins in the presence of Oxone
  作者：Soumen Payra、Navin Yadav、Jarugu Narasimha Moorthy

  DOI：10.1039/d1nj04892a

  日期：——

  The reaction between aryl olefins and thiols in the presence of Oxone in toluene–water (9 : 1, v/v) affords β-hydroxy-2-arylethyl aryl sulfides smoothly by the interception of intermediary thiyl radicals with aryl olefins; the former are generated by the oxidation of thiols with Oxone in a biphasic medium. However, the change of the solvent system to acetonitrile–water facilitates a nonradical and

  芳基烯烃和硫醇在 Oxone 存在下在甲苯-水 (9 : 1, v/v) 中的反应通过拦截中间硫基自由基与芳基烯烃顺利地提供 β-羟基-2-芳基乙基芳基硫化物；前者是通过在双相介质中用 Oxone 氧化硫醇产生的。然而，将溶剂系统改为乙腈 - 水促进了非自由基和协同途径，仅通过串联点击反应，然后氧化。本质上，在甲苯-水介质中促进了“氧化加成”，而在乙腈-水介质中促进了“加成-氧化”。鉴于 Oxone 易于获得、环境友好且价格低廉，溶剂介导的转换构成了对两种不同产品的轻松直接访问，即 β-羟基-2-芳基乙基芳基硫化物和 2-芳基乙基芳基砜。
• Fluoride ion induced reaction of phenylthiomethyltrimethylsilane (1) with aldehydes and ketones: a simple procedure for the formation of β-hydroxyphenylsulphides
  作者：John Kitteringham、Michael B Mitchell

  DOI：10.1016/0040-4039(88)85151-7

  日期：1988.1

  The tetra -butylammonium fluoride (TBAF) initiated reaction of pheny1thiomethyltrimethysilane (1) with aldehydes and ketones is reported. ß-Hydroxy-phenylsulphides are formed in good yields even with ketones that contain enolisable protons. In contrast, the reaction of the organosilane (1) with pyridine -oxide failed to give any 2-phenylthiomethylpyridine. Methy1thiomethyltrimethylsilane (4) was found

  据报道，由四丁基氟化铵（TBAF）引发的苯甲硫基甲基三甲基硅烷（1）与醛和酮的反应。ß-羟基-苯基硫化物即使以含有可游离质子的酮的形式也能以高收率形成。相反，有机硅烷（1）与吡啶氧化物的反应未能得到任何2-苯基硫代甲基吡啶。发现甲硫基甲基三甲基硅烷（4）对醛和酮的反应性低于（1），并且也无法与吡啶氧化物反应。已经研究了自由基清除剂对苄基三甲基硅烷与二苯甲酮和吡啶氧化物的氟化物引发反应的影响。